Ultrasound-assisted construction of novel diethyl {(4-oxo-1,4-dihydroquinolin-3-yl) (aryl/heteroarylamino)methyl}phosphonates using CdI₂ nanoparticles as an efficient catalyst: Synthesis, characterization, and antifungal properties

Abstract

The synthesis of some novel diethyl {(4-oxo-1,4-dihydroquinolin-3-yl)(aryl/heteroaryl-amino)methyl}phosphonates, was achieved. The methodology is based on one-pot three-component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (1), amine, and diethyl phosphite in the presence of CdI₂ nanoparticles as an efficient catalyst under conventional heating at 80 °C or ultrasound irradiation at 50 °C. The mild reaction conditions, operational simplicity, and excellent yields are the essential advantages of this protocol. Most of the products recorded inhibitory effects toward plant pathogenic fungi nearly to the standard control. The hybridization between diethyl α-aminophosphonate and quinolin-4-one moieties clubbed with sulfonamide, antipyrine, or 1,2,4-triazine in one molecular frame displayed good antifungal activities.

GRAPHICAL ABSTRACT

Keywords:

• α-Aminophosphonate
• quinolin-4-one
• CdI₂ nanoparticles
• Kabachnik–Fields
• ultrasound
• antifungal